Assessing the pKa-Dependent Activity of Hydroxyl Hydrogen Bond Donors in the Organocatalyzed Cycloaddition of Carbon Dioxide to Epoxides: Experimental and Theoretical Study

Prapussorn Yingcharoen, Chutima Kongtes, Sunatda Arayachukiat, Kittipong Suvarnapunya, Sai V. C. Vummaleti, Sippakorn Wannakao, Luigi Cavallo, albert poater, Valerio D'Elia

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

The development of hydrogen bond donors (HBDs) as catalytic moieties in the cycloaddition of carbon dioxide to epoxides is an active field of research to access efficient, inexpensive and sustainable metal-free systems for the conversion of carbon dioxide to useful chemicals. Thus far, no systematic attempt to correlate the activity of a diverse selection of HBDs to their physico-chemical properties has been undertaken. In this work, we investigate factors influencing the catalytic activity of hydroxyl HBDs from different chemical families under ambient conditions by considering the HBDs Brønsted acidity (expressed as pKa), the number of hydroxyls and structural aspects. As an effect, this study highlights the crucial role of the hydroxyl protons’ Brønsted acidity in determining the catalytic activity of the HBDs, identifies an ideal range for the hydroxyl HBDs proton acidity (9
Original languageEnglish (US)
Pages (from-to)366-373
Number of pages8
JournalAdvanced Synthesis & Catalysis
Volume361
Issue number2
DOIs
StatePublished - Nov 26 2018

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